“PLAY THE MAN, NOT THE CARDS” Why it Pays to be Like Harvey Specter

This is a poker mantra that has recently shown up on the TV show, Suits and is a favorite saying of one of the lead characters, attorney Harvey Specter.   If you have never seen the show, Harvey is the top business litigation attorney at a NYC law firm and he charges $1,000 per hour – you want him on your side.  The. Guy. Does. Not. Lose.  Harvey makes it a point to know who he is going up against – and always has his talented associate learn about their history, dig up their dirty laundry, and in general he always tries to know exactly what he is dealing with and he is going to face.  He is sometimes surprised, but he is never unprepared.

Why am I telling you this?  It’s not to get you to watch Suits – even though the show is excellent.  My point is that you have to know your audience – you have to pay attention to the situation you are walking into and prepare for it.

Fall Pitch Night in Boston

I am on the screening committee for a local, Business school alumni-based Angel organization in Boston and we recently had its Fall pitch night.  We carefully screen a number of companies who pitch to the screening committee on a Saturday, and then present a small number of these companies to our Angel investors about a week later.  This past round yielded some exceptional companies with amazing, proven teams.  We were excited to show them to our investor pool.

The pitches were polished, the slide decks looked great, and the teams knew their material.  However, only one investor showed interest in either company.  Just one.  Objectively – these were among the best companies we had ever shown to our investor base.  So what happened and why?

Company #1

The first company was pitching a mobile app that allows young women to look at a large number of “big, beautiful” photos of up-to-the-minute fashions.  Users are allowed to do the “tinder-swipe” to decide if they loved the fashion or not.  Beta testers could not put this app down and spent dozens of hours rating new fashions in a game-like environment.  The team was impressive – a talented developer with 2 recent exits of mobile app companies – including one that was sold to Facebook.  This guy knows how to build a sticky app AND how to sell it.   One investor half-raised their hand to show he was interested.

Company #2

The second company was an online dating site that allows women to post men (co-workers, brothers, friends) in their lives onto the site with an endorsement so that other women can have a “validated lead” and an objective opinion of a guy on the dating site.  That viewer would then contact the female poster to ask her about her male friend.  This approach actually eliminates a few of the pitfalls of online dating, and the team has a huge amount of experience in the online dating space.  They too had a successful prior exit, and it was obvious – after 2 minutes – that these folks know the space inside and out and found a great solution to offer online daters.  Again – great pitch, great team, no interest.

What Happened?

The angel group was comprised entirely of men.  All men over 50.  A bunch of men wearing blue blazers, khaki pants, and loafers.  They all attended one of the most prestigious business schools in the nation, are successful accredited investors and have an interest in putting that money to work.   But every single one was an older white man.  I watched the investors visibly struggle during the presentations and although they listened with interest – they were clearly lost.  They did not have the slightest idea what the entrepreneurs were talking about half the time.

Why?

You see, the target demographic for the mobile app is young fashion-forward women aged 16 to 25.  The target audience for the dating site is 26 to 35 year old females looking for serious relationships.  I saw their curious expressions when the presenters talked about the app and the site and why the target audiences were so excited about them.  The older men could not relate in the least.  I’m guessing that even though many of them probably had daughters that age, they did not understand their fashion social media habits or online dating frustrations.  These men don’t know about how Zara utilizes a lightning-fast inventory creation and turn model (they’ve probably never even hear of Zara) and how female match.com users get tons of daily emails from creepy men.

What Went Wrong?

The presenters might as well been speaking pig Latin.  They did not to relate to their audience, nor were they able to talk in terms and explain their business concepts in words and language with analogies that their audience would understand.  This is a huge miss. If your potential investors don’t understand what you do they won’t understand your concept and they definitely won’t consider taking a meeting with you.

Don’t Make this Mistake

You need to channel your inner Harvey Specter.  Dig up some dirt, do your homework and know about the situation you are walking into.  When you are pitching to the “Harvard Business School Angels” , before you walk in the room, you might want to think about the fact that your audience most likely doesn’t read Vogue or swipe left or right on Tinder,  then adjust your delivery accordingly!!

By the way, if you didn’t notice, I made sure to explain who Harvey Specter was because I’m not sure that every readier of this article watches Suits.

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